How To Founder

You sold your company. The wire cleared. Six months later, you're more anxious than when you were working 80-hour weeks.

Most founders spend years planning their exit strategy and zero hours planning what happens the day after the deal closes. Tom Freiling led a digital publishing company to NASDAQ, sold it, then launched into his next venture without taking a breath. Looking back, he calls it his biggest mistake. The problem wa...

Your benefits broker just bought a boat. You paid for it.

Mid-size companies waste an average of eighteen hundred fifty six dollars per employee annually on hidden broker fees their advisors never disclose. These aren't mistakes. They're business models built on your ignorance. When your broker's compensation rises with your costs, fiduciary duty dies. They'll smile, bring donuts to enrollment meetings, and quietly c...

You bought the expensive firewall. You paid for the certifications. You still wake up wondering if one phishing email could wipe you out.

Most founders throw money at cybersecurity like it's insurance against catastrophe. They stack tools, chase compliance badges, and assume more spending equals more protection. Meanwhile, the three attack vectors responsible for 82% of breaches sit wide open because they're boring to fix an...

When was the last time you made a business decision before asking what it costs in taxes?

Most founders design their operations first, then call their accountant in March to calculate the damage. They hire in July, buy equipment in November, distribute profits in December, and never consider tax implications until the bill lands. Mike Jesowshek spent a decade watching entrepreneurs bleed five figures annually, not from missing deduc...

What if that pit in your stomach before a difficult conversation isn't weakness—it's wisdom? Most founders think nervousness before hard talks signals they're unprepared. The reality? Zero anxiety means you're about to be too harsh or unclear. That discomfort is your nervous system telling you the stakes are real and the relationship matters. In this episode, we break down why calibrating your emotional state—findin...

Why do the processes you create end up ignored? You document workflows, create templates, build systems—and then nobody uses them. The problem isn't discipline. It's design.

Most founders treat processes like chores instead of products. They skip user research (who's actually using this?), ignore usability (can someone follow this under pressure?), and never iterate. Colin Gray turned this around by building The Podc...

What if everything you know about authentic leadership is wrong?

In this eye-opening episode, we sit down with executive coach Andrew Poles, a 3x founder who's guided over 10,000 leaders worldwide. Discover why the "authentic you" who got you here won't get you there, how elite founders rehearse their leadership character like actors prep for Broadway, and the exact moments you need to perform confidence you don...

What if the moment you finally exhale is the moment your business starts to die?

This raw, unfiltered conversation between Chris Franks, Anthony Franco, and Stephanie Hays tackles the uncomfortable truth most founders avoid: success breeds complacency, and complacency breeds failure. They dissect why seventy-three percent of midsize companies plateau within three years of hitting profitability, explore the addictive nature of startu...

Ever wonder if you're the bottleneck in your own business?

According to MIT Sloan Management Review, fifty-eight percent of executives admit their leadership approach hasn't evolved with their organization's growth stage. What worked brilliantly at five employees creates chaos at fifty. In this revealing episode, we sit down with Dr. Christiane Schroeter—TEDx speaker, top one percent podcaster, and leadership coach with ...

Your obsession with flawless execution might be the very thing holding your company back.

Most founders rise to leadership because they're exceptional operators—they solve problems faster, think deeper, and deliver better than anyone else. But here's the uncomfortable truth: those same skills that made you invaluable as an individual contributor actively work against you as a leader. In this episode, Andrew Poles, three-time...

Are you about to waste six months pitching investors who'll never bite?

Most founders confuse hope with readiness—they chase funding before the metrics prove they deserve it. The gap between "we should raise" and "we're ready to raise" costs founders equity, momentum, and credibility. This episode breaks down the exact signals that separate wishful thinking from genuine round readiness.

Drawing on insights...

What if the key to survival isn't cutting costs—it's spending smarter?

Most founders facing a cash crunch default to slash-and-burn mode, gutting their teams and operations in a panic. But CB Insights reveals that thirty-eight percent of failed startups died not from spending too much, but from cutting the wrong things at the wrong time. When DataVox CEO Pete Caputa faced six months of runway, he did the unthinkable: he doub...

What if chasing the latest software stack is sabotaging your business?

In this revealing episode, we sit down with Lucas Erb, founder of AIExperts.com and former Deloitte consultant, who challenges everything founders think they know about technology decisions. Discover why enterprises waste 38% of their IT budgets on redundant software, how Shopify's "boring" technology choice saved years of migration pain, and why yo...

What if the brand guidelines you're protecting are actually killing your growth?

Most founders treat their brand like a museum piece—something to preserve rather than evolve. But Aurora Winter, who's built multiple seven-figure companies and authored "Turn Words Into Wealth," reveals why that approach is costing you customers, capital, and competitive advantage. In this conversation, she breaks down the neuroscienc...

Most founders think a solid operating agreement will save their partnership. It won't.

Travis Lee Howard—ten-time founder, conscious leadership expert, and former partnership attorney—joins us to reveal why sixty-five percent of startups fail not because of market problems, but because founders don't know themselves well enough to work together. He shares the "gift versus gift giver" framework that helped him navig...

What if your relationship with money is why your business isn't growing?

Most founders track revenue obsessively while their companies hemorrhage cash. The real problem isn't in the spreadsheets—it's in your head. Dr. Travis Parry reveals the four psychological money scripts that secretly drive every financial decision you make, from childhood programming you didn't know existed. Whether you worship money, avoid it, ...

What if your fear of rejection is costing you deals you've already won?

In this no-holds-barred episode, Chris Franks and Stephanie Hays tackle the closing conversation that makes most founders squirm. Discover why traditional closing techniques are dead, how to spot the difference between real objections and buyer stalls, and the simple transition phrases that turn awkward silences into signed contracts. This isn't about ma...

What if the key to outmaneuvering both scrappy startups and sluggish enterprises lies in mastering the messy middle?

Join us as we dive deep with Sardor Umrdinov, founder of Home Alliance, who scaled from $800 to a nationwide powerhouse with over 10,000 service locations. Discover why mid-market companies (between $10M-$1B revenue) represent only 3% of businesses yet drive 33% of U.S. private sector GDP. Learn the brutal truth about...

What if everything you think you know about rebranding is wrong?

In this no-nonsense episode, we tackle one of the most misunderstood topics in business: when to rebrand versus when to resist the urge. With a shocking 73% of rebranding initiatives failing to deliver measurable ROI within two years, we dive deep into why most founders get this decision spectacularly wrong. Discover the real reasons companies like Jaguar and Cracker B...